Minding The Gap When I Was 14 And Just Starting Out

Part One: Minding The Gap When I Was 14

Being an entrepreneurial mind means constantly coming up to gaps. Places where we don’t know what to do or how to do it.

When I set out on this entrepreneurial journey when I was 14, I had no idea what I was doing. Do you have that feeling sometimes?

I knew that all my friends wanted to borrow my clothes and I had a feeling I could make some money off of it. But, I had no one to tell me how to do it. I had reached a big, dark, scary gap in where I was versus where I wanted to be. A big large gap in what I knew how to do versus what I wanted to do.

Teachers and school counselors couldn’t help me. My friends didn’t understand what I was talking about (and they were my intended customer). And, I didn’t tell my family in fear that they would not be happy with the idea that I would make money off my friends.

I had to leap over that gap and hope that what I did as my feet left the ground worked. I remember being so nervous and so unclear.

The first time I said to a friend, “yes, you can rent my clothes, here is my rate card.”  I questioned myself. Is that what I should say? Too formal?

I wished someone could at least share with me how to think about this. Should I write out a plan? What’s on a business plan?

I stumbled a lot along the way and made some mistakes, big and small. I tried some things that worked better than I expected and some that totally bombed.

That summer in 1980 –something I rented out my clothes to my customers…I mean friends.

There was nothing left for me to wear – but I had a lot of cash in my lock box under my journal. I definitely would have gone smoother with a little guidance but in the end I made $1,376.50 which wasn’t bad for a scrawny kid with big hair. I think the late fees really helped!

tamara kleinberg top entrepreneur innovator The Shuuk

(look what I found tucked away in my closet…my original rate card)


I share my 80s pegged pants, feathered hair, padded shoulders story because as entrepreneurial minds you are also hitting big, scary gaps. How you propel yourself over those gaps can be daunting and eerily overwhelming.

As entrepreneurial minds and disruptive innovators we kind of like carving our own paths. It’s part of the thrill. But, wouldn’t it be great if you could at least get a map, a compass and a water bottle as you set out on this journey. A little something to help you along the way?

I know my 14 year old self really wanted that guidance. You are my peeps so I won’t leave you hanging. More to come on Friday on how I got a little help along the way and made my first business a success…

For now, I wanted to share my pain and hear your thoughts. What gaps do you hit? How do you deal with the unknown? What type of guidance would help you? Create some magic and share in the comments section below.

Part Two: What I Did When I Reached A Gap

Secret look

Secret look

As I mentioned above, I did pretty well with my first business in 1980something. But, I didn’t do it all on my own. Well kind of, but part of the process was figured out what the heck to do. I knew I didn’t have all the answers so I decided I needed to learn from others. I decided to stalk some innovative people. No I didn’t go through anyone’s trash but I did get up close and personal to learn a few lessons. 

Ok, back to 1980something. I figured if I watched what they did I could transfer those learnings over to my entrepreneurial idea. Here are the three people I stalked and what I learned from them. A quick note, this is pre-internet days so there were no websites, blog posts or googling it, so try not to laugh


1) My dad. At the time he owned a resort. I spent most days after school, weekends and in the summer working and playing there. My dad was (and still is) a master marketer. I’d listen to how he talked to potential hotel guests and take notes. I noticed that when referring to the room prices he would say, “let me refer to my rate card.” I noticed that when he did this, people didn’t argue about the price. It was as if having a rate card set things in stone. Hence, I created a rate card. 

2) The clothing boutique down the street. There are a million clothing stores to choose from but this one was my go-to. While browsing one day the shop owner, Jill, came over and said, “I put some clothing I think you’ll like in your dressing room.” What?! She used my past purchases to recommend clothing to me that I may not have seen if she hadn’t pulled them out. Amazon, Zappos, Fabletics and all the online retailers do this now. They put what you will probably like front and center for you and so did I. I would lay out outfits before my friends came over. Most of the times they rented the entire outfit.

3) TV. I know this one sounds a little weird, especially because I don’t even have cable now but back then TV commercials were it. I would spend hours watching and taking notes on which commercials caught my attention, which ones made me want to buy the product and which ones sucked. Most commercials were excuses for bathroom and snack breaks, but every now and again I would see a commercial that was worthy notes. Doing this helped me create my first tagline,


Wear Today’s Fashion That Won’t Take Up All Your Allowance.


Ha! Sounds kind of funny now but it was a good try based on what I learned from stalking. 


Now, many years later, I still stalk people. If you are doing something innovative I am stalking you. I am reading your blogs, subscribing to your site, checking out your website, etc. If you stalk innovative people you have no choice but to up your own game. And when you hit those gaps, you’ll have some ideas for how to deal with them. 


Find 3 people that you think are innovative and can teach you something and go stalk the heck out of them.


Who do you stalk? What have you learned from stalking innovative people?  Create some magic and share in the comments section below


Take the Online Assessment and Discover Your Unique Innovator Archetype



5 Responses to “Minding The Gap When I Was 14 And Just Starting Out”

  1. Kenny H. says:

    I totally feel the pain right now. Glad to know I’m not alone. Yes the roller coaster ride is exciting but boy a little help goes a long way. You asked what would help me? What are the key elements i need figured out before I launch. I know I’ll figure out a lot along the way but would would help me start.

  2. Laura Ollinger – New York says:

    I have so many gaps. When I get those I seek out people I know have been through it and try to get their advice. That’s why I’m on The Shuuk. I love the new inventions and I spend a lot of my time watching and learning from Tamara and the other people here. Watch and learn I guess, that’ show I mind the gaps.

  3. Helen says:

    Oh my gosh, I feel this way every day. Thank you so much for reminding me that it’s totally normal to not know what you are doing. I can’t wait to hear how you solved it. For guidance, since you asked, I would like some guidance around how to set myself apart from my competition. It seems like I have new competition daily. Thank you!

  4. Brian Telly says:

    Up and down for me on this one. Sometimes I feel like this and other days I feel like I know it all. Not sure if either is ever true…ha ha ha ha!

  5. Tommy Granger says:

    So many gaps! I have an amazing mastermind group. They don’t have all the answers but they do help me think about the issues and find possible solutions. I think it’s important to surround yourself with clever people. I could use some help on how to get buy in for my ideas. Sometimes it feels like I have an idea that is brilliant and no one else gets it.